In this episode of the Power Producers Podcast, host David Carothers, co-host Kyle Houck, and returning guest Kevin Ring of the Institute of Work Comp Professionals come together for a special tribute to the legacy of an industry pioneer, Preston Diamond. The conversation is sparked by the release of “The Diamond Playbook,” a new book compiling decades of Preston Diamond’s influential weekly sales letters. Kevin shares the story behind the book’s creation and offers a deep dive into Preston’s timeless sales philosophy: being client-centric, using stories to build trust, and moving beyond a product-pushing mentality. They also discuss how Preston’s critiques of agency websites from the 1990s are still shockingly relevant today.
Honoring a Legacy: The Diamond Playbook
Kevin Ring details how the Institute of Work Comp Professionals discovered a massive archive of Preston Diamond’s weekly sales letters, which began as a fax broadcast, and compiled them into a book. The project was a surprise tribute to honor Preston’s immense and ongoing contribution to the insurance industry and the thousands of agents he has mentored.
The conversation centers on the core of Preston’s teachings: never be product-centric. Instead, agents must first focus on understanding a client’s needs, wants, and fears. By building a relationship of trust and using powerful stories to explain complex concepts, the insurance sale becomes a natural and easy conclusion to a value-driven conversation.
A fascinating takeaway is an essay Preston Diamond wrote in the 1990s critiquing agency websites. Kevin and David discuss how his gripes—that most sites are just static “electronic business cards” instead of powerful tools for establishing expertise and credibility—are just as true today, highlighting a persistent missed opportunity for many agencies.
The episode revisits another of Preston’s core tenets: focus on deepening relationships with existing clients. They discuss the immense, low-hanging fruit available by rounding out accounts (“client share”) and networking clients with each other. This creates powerful exit barriers and demonstrates a level of value that goes far beyond just placing a policy.
In commercial insurance, the most dangerous threats to your book of business aren’t always visible on the loss runs. One of the most overlooked vulnerabilities for middle market producers is ignoring the personal lines needs of their business owner and executive clients.
In an industry where tradition often outweighs innovation, artificial intelligence and automation are slowly but steadily reshaping how independent insurance agencies operate. The push toward smarter, more efficient workflows is no longer a matter of if—but when. While many agencies are still evaluating how AI fits into their operations, early adopters are already reaping the benefits of streamlined submissions, faster processing, and actionable data insights.
The commercial insurance industry is changing faster than ever—and not always for the better. Consolidation is accelerating. Service levels are declining. Private equity is pushing agencies to scale in ways that strip out the personal touch that once defined the independent channel. But for the producers willing to do the work, lean into mentorship, and sharpen their craft, this isn’t a challenge—it’s an opportunity.
The commercial insurance industry is in the midst of a major evolution. The traditional workflows that once drove agency productivity are now dragging down growth, overloading staff, and frustrating owners who are trying to scale efficiently. For independent insurance agencies—especially those in the middle market—adapting to these challenges without increasing overhead is a tightrope walk.
Few industries reward consistency, discipline, and patience quite like middle-market commercial insurance. Initially, every producer starts with a different story, background, and path into the business. However, the ones who rise are the ones who learn to embrace the long game. Moreover, while success may take time, those who persevere ultimately reap the benefits. Furthermore, this industry values resilience, and those who remain committed often find themselves achieving great success in the end.
In today’s performance-obsessed culture, achieving elite status in your profession can often come with a hidden price. Tania Khazaal, known to many as Tanya the Herbalist, knows this truth firsthand. After climbing the ranks in the insurance industry and landing in the top 1% of sales professionals, she found herself at a crossroads. Despite the accolades, international travel perks, and consistent recognition, she was suffering from a quiet crisis: burnout.
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